Trail Running calendar near Burlington 2026-2027

An ultramarathon in Van Cortlandt Park featuring an initial flat lap plus ten cross country loops, stocked aid stations, drop bag access, and finisher awards including a medal, singlet, meal and post race beer.

A 12 mile technical out and back trail race on the Holyoke Range near Amherst, MA, with more than 3,500 ft of elevation gain. Rocky singletrack ridgelines, two manned water stations, and registration currently shows full with a waitlist.

The A Run to Remember will take place in Red Hook on Saturday 2 May 2026. You can run between 5 and 10 kilometers.

Rock The Ridge is a fundraising trail event at Mohonk Preserve on May 2, 2026. Options include a 50 mile ultra, a 26.2 mile trail marathon and relay teams, with proceeds supporting conservation and education.

Trail races at Bear Mountain State Park on May 2, 2026 include 10K, half marathon and 50K over singletrack with technical sections, rolling climbs, tree cover, rocky and muddy terrain and occasional stream crossings.

Run a flat one mile course in Van Cortlandt Park while wearing your own inflatable costume. This unique Bronx event supports charity and takes place during a local ultramarathon for a high energy atmosphere.

Celebrate National Truffle Day with a chocolate themed trail run at Giddings Park. This event features a three loop 5K for all ages and a kids fun run to support Franklin Elementary School programs.

A technical trail half and full marathon at University Settlement Camp in Beacon, NY on May 3, 2026, featuring steep, exposed climbs and substantial elevation gain with official aid stations and strict cut-off times.

A technical out and back 50K on New Haven blue trails with about 6,350 feet of climbing, strict time cutoffs, no crews or pacers, and multiple aid stations including water only stops.

Experience a trail run or walk through the campus of The Hartsbrook School in Hadley. Choose between a 5k or a 1 mile race on natural terrain while supporting local land stewardship and agricultural education programs.

Trail races in Lyme, Connecticut offering a 9.2 mile loop and a 3 mile sprint on Mount Archer trails. Chip timed and rain or shine, with 100% of proceeds donated to local emergency services.

This community trail run on Clausland Mountain honors caregivers and supports mental health and sobriety causes. Participants take on a 3.75-mile historic course, receiving a medal in an event focused on gathering, not competition.

Run for a cause at the Bruynswick Winery Run, a 6k cross-country race benefiting the Ulster County SPCA. Enjoy a scenic course at the foot of the Shawangunk Ridge, with music, drinks, and a chance to meet shelter animals. Free children's da..

Experience the eighth annual Spring Fling 600 trail races at YMCA Camp Sloper. Choose between a 6 mile race or a 10 hour challenge to complete as many loops as possible on a scenic three mile course.

A community event on May 9, 2026 featuring a Family Color Run and a 5K Trail Run at Hamden and New Haven YMCA locations. Registration runs from Feb 20 to May 8 with entry fees of $10 and $30; first 100 pre-registrants receive a Y giveaway.

A 9-hour timed trail event in Roosevelt Forest, Stratford, CT featuring a 2.2-mile loop with 131 feet of climb per lap, a 50-runner limit, pavilion aid station, and awards for most miles completed.

A last person standing loop race on Ragged Mountain where runners repeat a roughly 3.11 mile loop and must finish each lap within one hour; entrants are eliminated if they fail to start or finish a lap, continuing until a single finisher re..

The Free Spirit 50K is a scenic ultra on the dirt roads of Leyden, Massachusetts. The route passes historic farms, forests, and a vintage covered bridge, offering a classic New England countryside experience.

Annual May races on the Ashuwillticook Rail Trail offering marathon, half and 8K distances starting and finishing at the Adams Visitors Center. Proceeds support the rail trail and a municipal fund for the City of Pittsfield.

Tails & Trails State Forest Run in Pittsfield State Park on May 16, 2026 features 50K, 25K and a 5 mile loop of single track, pine forests and mountain bike style trails while supporting local animal rescues.